I'm on a client site this week upgrading TFS 05 to TFS 08 and unlike my previous installation, this one has not been quite as smooth. 

Server Setup

A brand new shiny server was proived for the update (dual quad core with 4Gb of ram).  Initially we had tried to install on another similar server that had some other software on it for their helpdesk.  Unfortunately, the install of TFS 05 or WSS 2 or both screwed this software and we had to restore the server and leave it alone.  Not good!

Lessons learnt 

1) don't expect any useful support from Symantec - Support guy:  "Sorry but that is not one of our products", Me: "Ahhh, but I downloaded a trial version from your web site!".

2) don't install TFS (05) onto a server running anything that uses SQL Reporting or the default web site or WSS (2 or 3).  I fact, it's way simpler to have a clean server.

Moving

I neglected to check that TFS SP1 was installed on the old server before configuring the new server with SP1 so I had to update the old server then redo the backups.  No biggy, but it meant sitting arond for an hour.

Then the fit hit the shan.  After 3 hours trying to figure out why the restorative move process was giving me stupid TFS errors I realised the TFS 05 installation media I was using was for the Workgroup edition.  Dur!  Luckily, it was a simple matter of removing WSS2 and TFS 05 then running through the process again (for the 4th time) with the correct installation.

At the end of this everything was working apart from SQL Reports - which I ignored as it was late in the day.

I then upgraded TFS 05 to TFS 08 which tool another hour, tested and I was done!

Lessons learnt

1) Make sure the source and target TFS installations are patched to the same levels.  Same goes for WSS.

2) Make sure the installation media is the correct version/edition!

3) Create and save the DB restore scripts the first time you do it - it gets borng very quickly having to redo the restore 4 times using the SQL Management Studio GUI.

SharePoint

Thanks to a useful blog post I felt a lot more comfortable about attempting a SharePoint upgrade.  The customer had not done any customisations to the project portal site so the prescan ran without issue and the upgrade comlpeted without errors.

Lessions learnt

1) An inplace upgrade is ok if the prescan is completely clean and you have experts available to help (or google).

Other Tips

I had made a binder with all the documentation I needed, including the Move instructions from MSDN, the TFS P&P Guide (all 500 pages), the licensing white paper, my upgrade plan - including the steps, servers, logins and other site relevant information - and a DVD with the software I needed in case the client could not find something (next time I'll check the DVD works tough as the TFS 08 iso was corrupt - thankfully the client had this).  I'll leave this binder with the client as a parting gift :)

I'm not quite done yet, I still need to configure some build scripts.. will update this post later.